Tag: M.W=100-200

Reference of 112-27-6, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 112-27-6, name is 2,2′-(Ethane-1,2-diylbis(oxy))diethanol. A new synthetic method of this compound is introduced below.

Triethylene glycol (30 g, 0.2 mol) was dissolved in a solution of NaOH (8 g in 8 mL of H2O) and stirred for 10 min. Then benzyl chloride (7 mL, 0.062 mol) was added and the reaction mixture was heated to 100 C. and stirred overnight. The crude reaction was diluted with sat NaCl (500 mL), washed CH2Cl2 (2×400 mL), organic layers dried MgSO4, and evaporated to dryness. Column chromatography (silica, ethyl acetate to ethyl acetate/MeOH, 10:1) afforded 1 a yellowish oil (9.87 g, 67% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,112-27-6, 2,2′-(Ethane-1,2-diylbis(oxy))diethanol, and friends who are interested can also refer to it.

Reference:
Patent; James, Kenneth D.; US2008/207505; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 637031-88-0, 3,3-Difluorocyclobutanol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 637031-88-0, blongs to alcohols-buliding-blocks compound. SDS of cas: 637031-88-0

1-Bromo-4-(3,3-difluorocyclobutoxy)benzene. PPh3 (267 mg, 1.02 mmol) is dissolved in dry toluene (2 mL) and cooled to 0 C. Dropwise, diethyl azodicarboxylate (0.165 mL, 1.02 mmol) is added and the light yellow sol. is stirred at 0 C for 10 min. A sol. of 3,3-difluorocyclobutanol (100 mg, 0.925 mmol) in toluene (0.8 ml) is added. After stirring for another 10 min at rt, 4-bromophenol (160 mg, 0.925 mmol) is added, and the sol. is stirred at 100C overnight. The mixture is allowed to cool to rt, and the solvents are removed under reduced pressure. Purification of the crude by automated FC (Combiflash, 40 g silicagel, EtOAc / heptane 0:100 ? 5:95) yields the title product. LC-MS: tR= 0.94 min (conditions 3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,637031-88-0, its application will become more common.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BEZENCON, Olivier; GATFIELD, John; HEIDMANN, Bibia; SIEGRIST, Romain; STAMM, Simon; (86 pag.)WO2016/41892; (2016); A1;,
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Related Products of 108343-90-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 108343-90-4, name is 2-Amino-2-(2-methoxyphenyl)ethanol, molecular formula is C9H13NO2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a suspension of HOBt (3.24 g, 23.9 mmol) and WSC (4.60 g, 23.9 mmol) in THF (40 mL) under nitrogen atmosphere, 36 (1.90 g, 11.4 mmol) and 18c (1.29 g, 7.4 mmol) were added. The reaction mixture was stirred at room temperature for 24 h and the solvent was evaporated under reduced pressure. The crude product was dissolved in ethyl acetate, the solution washed with NaHCO3, HCl 2 M and brine, dried over Na2SO4 and evaporated under reduced pressure to afford 37 as a white solid (2.33 g, 97%); mp 93-95 C. 1H NMR (CDCl3) delta: 7.64 (1H, d, J = 8.3 Hz), 7.21-7.43 (5H, m), 7.15 (1H, m), 6.29-7.03 (2H, m), 6.90 (1H, s), 5.51 (1H, m), 4.05 (3H, s), 3.93-4.03 (2H, m), 3.93 (3H, s). 13C NMR (DMSO-d6) delta: 162.1, 156.9, 138.9, 132.9, 129.4, 128.6, 127.6, 126.2, 124.0, 122.0, 120.8, 120.7, 111.3, 111.0, 105.1, 63.8, 56.0, 50.9. Anal. Calcd for C19H20N2O3: C, 70.35; H, 6.21; N, 8.64. Found: C, 70.30; H, 6.27; N, 8.60.

According to the analysis of related databases, 108343-90-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Cananzi, Salvatore; Merlini, Lucio; Artali, Roberto; Beretta, Giovanni Luca; Zaffaroni, Nadia; Dallavalle, Sabrina; Bioorganic and Medicinal Chemistry; vol. 19; 16; (2011); p. 4971 – 4984;,
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Reference of 558-42-9, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 558-42-9 as follows.

Example 221-{4-[6-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxy]-piperidin-1-yl}-2-methyl-propan-2-ol dihydrochlorideTo a solution of 3-butyl-4-(4-cyclohexyloxy-phenyl)-6-(piperidin-4-yloxy)-pyridazine dihydrochloride (Example 14, 0.2 mmol, 97 mg) in EtOH (2 mL) was added 1-chloro-2-methyl-2- propanol (0.4 mmol, 44 mu), and potassium carbonate (0.6 mmol, 83 mg). And the mixture was stirred at 50°C for 4 hours. It was then diluted with water/EtOAc. The organic layers were combined, dried, and condensed in vacuo and the residue was purified by silica gel chromatography (DCM to DCM + 10percent MeOH) to give a colorless sticky solid, which was dissolved in DCM (2 mL), 1 N HCI in ether (2 mL) was added, kept at room temperature for 10 min, condensed, triturated with hexanes to yield 1-{4-[6- butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxy]-piperidin-1-yl}-2-methyl-propan-2-ol dihydrochloride (86 mg, 77percent yield). LCMS: m z 483 [M+1]. 1 H NMR (400 MHz, CD3OD): delta 7.53 and 7.62 (1 H, s), 7.41- 7.46 (2H, m), 7.10 – 7.14 (2H, m), 5.42 – 5.52 (1 H, m), 4.41 – 4.46 (1 H, m), 3.65 – 3.83 (2H, m), 3.25- 3.47 (3H, m), 3.05 – 3.12 (2H, m), 2.22 – 2.55 (5H, m), 1.98 – 2.03 (2H, m), 1.78 – 1.83 (2H, m), 1.40 – 1.63 (7H, m), 1.38 (6H, s), 1.22 – 1.36 (3H, m), 0.81 (3H, t).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,558-42-9, its application will become more common.

Reference:
Patent; TRANSTECH PHARMA, INC.; GOHIMUKKULA, Devi, Reddy; JONES, David; QABAJA, Ghassan; ZHU, Jeff, Jiqun; COOPER, Jeremy, T.; BANNER, William, Kenneth; SUNDERMANN, Kurt; BONDLELA, Muralidhar; RAO, Mohan; WANG, Pingzhen; GOWDA, Raju, Bore; ANDREWS, Robert, C.; GUPTA, Suparna; HARI, Anitha; WO2011/103091; (2011); A1;,
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As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 27489-62-9, name is trans-4-Aminocyclohexanol, molecular formula is C6H13NO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. COA of Formula: C6H13NO

The aryl fluoride (2 g, 10.6 mmol) was placed in a 100 ml round-bottomed flask and stirred in 20 ml acetonitrile at room temperature. Potassium carbonate (3.3 g, 23.9 mmol, 2.2 eq) and 1,4-trans- amino-cyclohexanol (1.34 g, 11.6 mmol, 1.1 eq) were added and the mixture was then heated at 90 C overnight. The mixture was cooled to room temperature and then concentrated under vacuum. The crude material was purified by silica gel chromatography using 20 – 40 % ethyl acetate in petroleum ether to elute. The product-containing fractions were combined and concentrated under vacuum to provide 1 g (33 %) of the desired aniline as a yellow oil. (ES, m/z): [M+H]+ 285.0; NMR (300 MHz, DMSO): delta 8.04 (d, J = 9.3 Hz, 1H), 7.42 (d, J = 7.8 Hz, 1H), 7.06 (d, J = 1.8 Hz, 1H), 6.82 – 6.86 (m, 1H), 4.59 (d, J = 4.2 Hz, 1H), 3.39 – 3.49 (m, 2H), 1.78 – 1.94 (m, 4H), 1.18 – 1.32 (m, 4H).

With the rapid development of chemical substances, we look forward to future research findings about 27489-62-9.

Reference:
Patent; MERIAL INC.; LONG, Alan; WILKINSON, Douglas, Edward; (224 pag.)WO2016/118638; (2016); A1;,
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The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 28539-02-8, name is 1-(Hydroxymethyl)benzotriazole. This compound has unique chemical properties. The synthetic route is as follows. name: 1-(Hydroxymethyl)benzotriazole

To a solution of methyl 2-(2-(4-((6-methoxypyridin-3-yl)oxy)piperidin-1-yl)-3-methyl-5-oxo-5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)acetate (40 mg, 0.094 mmol) in THF (2 mL) was added lithium bis(trimethylsilyl)amide (47.1 mg, 0.281 mmol) dropwise at -70 C. After stirring for 15 min, a solution of (1H-benzo[d][1,2,3]triazol-1-yl)methanol (21.0 mg, 0.141 mmol) in THF (0.5 mL) was added dropwise and then stirred for 30 min at -70 C. The reaction was quenched with saturated aqueous NH4Cl (0.5 mL), treated with water (10 mL) and the mixture was extracted with EtOAc (20 mL*3). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by prep-TLC (100% EtOAc) to give the title compound. MS: 457 (M+1).

With the rapid development of chemical substances, we look forward to future research findings about 28539-02-8.

Reference:
Patent; BAO, JIANMING; GAO, XIAOLEI; KNOWLES, SANDRA L.; LI, I, CHUNSING; LO, MICHAEL MAN-CHU; MAZZOLA, Jr., ROBERT D.; ONDEYKA, DEBRA L.; STAMFORD, ANDREW W.; ZHANG, FENGQI; (214 pag.)US2017/183342; (2017); A1;,
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Related Products of 13330-96-6 ,Some common heterocyclic compound, 13330-96-6, molecular formula is C6H15NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

General procedure: To a solution of 6-substituted pyridazinone 9 (0.5 mmol) in DMF (10 mL) was added Cs2CO3 (0.55 mmol). An appropriately substituted nitro benzyl chloride (0.52 mmol) was added and the resulting mixture was stirred at 40-50 C for 3 h, the solvent was removed under reduced pressure and the residue was dissolved in EtOAc (30 mL), which was then washed with brine (3 × 10 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product, 2-nitrobenzyl-6-substituted-pyridazin-3(2H)-one (10), was used in the next step without further purification. To a solution of 10 in 95 % ethanol (50 mL) was added acetic acid (10 mmol) followed by slow addition of iron powder (2 mmol). The resulting mixture was stirred for 5 h at 100 C. The mixture was then filtered through celite and the filter cake was washed with 95 % ethanol (3 × 15 mL). The combined ethanol filtrates were evaporated in vacuo and the residue was re-dissolved in ethyl acetate (30 mL). The organic layer was washed with brine (3 × 10 mL) and 2 M NaOH (10 mL) sequentially. The organic layer was dried over anhydrous Na2SO4, evaporated in vacuo to afford 2-aminobenzyl-6-substituted-pyridazin-3(2H)-one (11) as a yellow solid, which was used without further purification. To a stirred solution of 11 and triphosgene (1 mmol) in dry dichloromethane (5 mL) was added triethylamine (2 mmol) under nitrogen atmosphere. A solution of the corresponding alcohol (1 mmol) in dichloromethane (5 mL) was added 5-10 min later and the mixture was stirred at room temperature overnight, diluted with dichloromethane (15 mL) and washed with water (3 × 20 mL). The organic phases were separated, combined, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by using column chromatography to afford the corresponding product.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 13330-96-6, 4-(Dimethylamino)butan-1-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xing, Weiqiang; Ai, Jing; Jin, Shiyu; Shi, Zhangxing; Peng, Xia; Wang, Lang; Ji, Yinchun; Lu, Dong; Liu, Yang; Geng, Meiyu; Hu, Youhong; European Journal of Medicinal Chemistry; vol. 95; (2015); p. 302 – 312;,
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Synthetic Route of 114686-85-0 ,Some common heterocyclic compound, 114686-85-0, molecular formula is C8H8Cl2O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

General procedure: The starting material, 2-(3,4-dimethoxyphenyl)-ethan-1-ol (521 mg, 2.86 mmol, 1.0 equiv) was dissolved in dichloromethane (20 mL) and imidazole (583 mg, 8.58 mmol, 3.0 equiv) was added. The mixture was stirred for 5 minutes. tert-Butyldimethylsilyl chloride (518 mg, 3.43 mmol, 1.2 equiv) was added and the reaction mixture was stirred at room temperature for 1 hr. Water (20 mL) and dichloromethane (20 mL) were added and the mixture was shaken in a separating funnel. The aqueous layer was separated and washed with dichloromethane (2 x 5 mL). The combined organic layers were washed with water (20 mL), brine (20 mL) and dried over MgSO4. Following filtration, the solvent was removed under reduced pressure. The crude material was purified by column chromatography on silica gel (eluting with a gradient from petroleum ether to 1:1 petroleum ether : ether) to afford 820mg of 1a (97%).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 114686-85-0, 2-(2,3-Dichlorophenyl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; O’Brien, Matthew; Konings, Lisette; Martin, Matthew; Heap, Jordan; Tetrahedron Letters; vol. 58; 25; (2017); p. 2409 – 2413;,
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Adding a certain compound to certain chemical reactions, such as: 7287-81-2, 1-(m-Tolyl)ethanol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Computed Properties of C9H12O, blongs to alcohols-buliding-blocks compound. Computed Properties of C9H12O

Procedure C. Variation of the substrate and the acylating agent in the CF3PIP-catalyzed kinetic resolutions. 1) The stock solution of the catalyst was prepared by dissolving 0.100 mmol of 2d (26.4 mg) and 3.75 mmol of N,N-diisopropylethylamine (6540L, 485 mg) in CHCl3 in a 5 mL volumetric flask and bringing the volume to the mark. 2) A one-dram vial was charged with 0.5 mmol of the racemic secondary alcohol and 0.500 mL of the stock solution of 2d, and cooled in an ice bath. After 15 minutes, 0.375 mmol of the anhydride was added. The mixture was swirled and left in the ice bath for a specified period of time, at the end of which it was quenched by rapid addition of 0.5 mL of methanol, allowed to warm slowly and left for one more hour at room temperature. The workup and chromatography were carried out as described in Procedure A.

The synthetic route of 7287-81-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Birman, Vladimir; US2005/256150; (2005); A1;,
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Reference of 111-46-6, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.111-46-6, name is 2,2′-Oxybis(ethan-1-ol), molecular formula is C4H10O3, molecular weight is 106.1204, as common compound, the synthetic route is as follows.

General procedure: Sodium hydride (60% dispersion in mineral oil, 0.5 equiv) wasadded portion-wise to a solution of triethyleneglycol (1 equiv.) inTHF (50 mL) under nitrogen. The reaction was stirred for 1 h andthen cooled to 0 C. Benzyl bromide (0.5 equiv.) was then addeddrop-wise, and the reaction mixture was warmed to room temperatureand then stirred for 16 h. The reaction mixture was cooledin an ice bath quenched by the addition of methanol (20 mL), andthen concentrated in vacuo. The residue was dissolved in DCM(30 mL), and washed with water (30 mL). The combined organicextracts were dried over anhydrous MgSO4, filtered, and concentratedin vacuo, to afford a yellow oil, which was purified by flashchromatography.

Statistics shows that 111-46-6 is playing an increasingly important role. we look forward to future research findings about 2,2′-Oxybis(ethan-1-ol).

Reference:
Article; Suthagar, Kajitha; Watson, Andrew J.A.; Wilkinson, Brendan L.; Fairbanks, Antony J.; European Journal of Medicinal Chemistry; vol. 102; (2015); p. 153 – 166;,
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